U.S. Pat. No. 4,025,638 to Gyurik discloses 5-cycloalkylthio- or oxy-2-carbalkoxyaminobenzimidazoles wherein the cycloalkyl is unsubstituted. These compounds are said to be generally useful for their anthelmintic properties.
U.S. Pat. No. 4,046,908 to Haugwitz et al discloses compounds of the structure ##STR2## wherein R.sup.1 is lower alkyl, phenyl-lower alkyl, halo-lower alkyl, mono-lower alkylaminoalkyl, di-lower alkylaminoalkyl, and alkyl pyridinium halide, R.sup.2 and R.sup.3 may be the same or different and are hydrogen or lower alkyl, R.sup.4 is cycloalkyl or cycloalkenyl which may include 1, 2, 3 or 4 halogen or lower alkyl substituents, and m is 0 to 3, n is 0 to 3, and m + n .ltoreq. 5, for their use as anthelmintic agents.
In addition, other benzimidazole compounds are known for their use as anthelmintic agents. For example, U.S. Pat. No. 3,574,845 to Actor et al, assigned to Smith Kline, discloses 5(6)-benzene ring substituted benzimidazole-2-carbamate derivatives including 5(6)-methylthio-2-carboethoxyaminobenzimidazole and various 5(6)-alkyl-2-carbomethoxyaminobenzimidazoles;
U.S. Pat. Nos. 3,929,821 and 4,002,640 to Beard et al and assigned to Syntex discloses various 5(6)-benzene ring substituted benzimidazole-2-carbamate derivatives including 5(6)-aralkylthio-2-carbomethoxyaminobenzimidazoles, such as, 5(6)-phenethylthio-2-carbomethoxyaminobenzimidazole.
U.S. Pat. Nos. 3,954,791 to Loewe et al and 3,928,375 to Duwel et al, disclose 2-carbalkoxy-amino-benzimidazole-5(6-phenyl and phenylthio ethers.
Other benzimidazoles useful as anthelmintic agents are disclosed in U.S. Pat. Nos. 3,929,822, 3,929,823, 3,929,824, 3,935,209, 3,965,113 and 4,005,202 all to Beard et al and assigned to Syntex; U.S. Pat. Nos. 3,682,952 to Actor et al, 3,578,676 and 3,694,455 to Dunn, 3,915,986 and 3,969,526 to Gyurik, all assigned to Smith Kline; and U.S. Pat. No. 3,738,993 to Haugwitz et al, assigned to Squibb.